Mavorixafor HCl

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522420

CAS#: 880549-30-4 (HCl)

Description: Mavorixafor, also known as AMD11070, AMD070, X4P-001, is an orally bioavailable and potent CXCR4 inhibitor. AMD11070 is an antagonist of SDF-1α ligand binding (IC50 = 12.5 ± 1.3 nM), inhibits SDF-1 mediated calcium flux (IC50 = 9.0 ± 2.0 nM) and SDF-1α mediated activation of the CXCR4 receptor as measured by a Eu-GTP binding assay (IC50 =39.8 ± 2.5 nM) or a [(35)S]-GTPγS binding assay (IC50 =19.0 ± 4.1 nM), and inhibits SDF-1α stimulated chemotaxis (IC50 =19.0 ± 4.0 nM). AMD11070 abrogates melanoma cell migration and is significantly more effective than AMD3100. AMD11070 represents a novel therapeutic strategy for both B-RAF wild-type and mutated melanomas.


Chemical Structure

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Mavorixafor HCl
CAS# 880549-30-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 522420
Name: Mavorixafor HCl
CAS#: 880549-30-4 (HCl)
Chemical Formula: C21H30Cl3N5
Exact Mass: 349.22665
Molecular Weight: 458.86
Elemental Analysis: C, 54.97; H, 6.59; Cl, 23.18; N, 15.26

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Related CAS #: 558447-26-0 (free)   880549-30-4 (HCl)    

Synonym: AMD11070; AMD-11070; AMD 11070; AMD-070; AMD 070; AMD070; X4P-001; X4P 001; X4P001; mavorixafor; Mavorixafor HCl; Mavorixafor trihydrochloride

IUPAC/Chemical Name: (S)-N1-((1H-benzo[d]imidazol-2-yl)methyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine trihydrochloride

InChi Key: FTHQTOSCZZCGHB-VLEZWVESSA-N

InChi Code: InChI=1S/C21H27N5.3ClH/c22-12-3-4-14-26(15-20-24-17-9-1-2-10-18(17)25-20)19-11-5-7-16-8-6-13-23-21(16)19;;;/h1-2,6,8-10,13,19H,3-5,7,11-12,14-15,22H2,(H,24,25);3*1H/t19-;;;/m0.../s1

SMILES Code: NCCCCN(CC1=NC2=CC=CC=C2N1)[C@H]3CCCC4=C3N=CC=C4.[H]Cl.[H]Cl.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 458.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Planesas JM, Pérez-Nueno VI, Borrell JI, Teixidó J. Studying the binding interactions of allosteric agonists and antagonists of the CXCR4 receptor. J Mol Graph Model. 2015 Jul;60:1-14. doi: 10.1016/j.jmgm.2015.05.004. Epub 2015 May 30. PubMed PMID: 26080355.

2: Cox BD, Prosser AR, Katzman BM, Alcaraz AA, Liotta DC, Wilson LJ, Snyder JP. Anti-HIV small-molecule binding in the peptide subpocket of the CXCR4:CVX15 crystal structure. Chembiochem. 2014 Jul 21;15(11):1614-20. doi: 10.1002/cbic.201402056. Epub 2014 Jul 2. PubMed PMID: 24990206.

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4: O'Boyle G, Swidenbank I, Marshall H, Barker CE, Armstrong J, White SA, Fricker SP, Plummer R, Wright M, Lovat PE. Inhibition of CXCR4-CXCL12 chemotaxis in melanoma by AMD11070. Br J Cancer. 2013 Apr 30;108(8):1634-40. doi: 10.1038/bjc.2013.124. Epub 2013 Mar 28. PubMed PMID: 23538388; PubMed Central PMCID: PMC3668477.

5: Mosi RM, Anastassova V, Cox J, Darkes MC, Idzan SR, Labrecque J, Lau G, Nelson KL, Patel K, Santucci Z, Wong RS, Skerlj RT, Bridger GJ, Huskens D, Schols D, Fricker SP. The molecular pharmacology of AMD11070: an orally bioavailable CXCR4 HIV entry inhibitor. Biochem Pharmacol. 2012 Feb 15;83(4):472-9. doi: 10.1016/j.bcp.2011.11.020. Epub 2011 Nov 28. PubMed PMID: 22146583.

6: Kawatkar SP, Yan M, Gevariya H, Lim MY, Eisold S, Zhu X, Huang Z, An J. Computational analysis of the structural mechanism of inhibition of chemokine receptor CXCR4 by small molecule antagonists. Exp Biol Med (Maywood). 2011 Jul;236(7):844-50. doi: 10.1258/ebm.2011.010345. Epub 2011 Jun 22. PubMed PMID: 21697335; PubMed Central PMCID: PMC3900290.

7: Parameswaran R, Yu M, Lim M, Groffen J, Heisterkamp N. Combination of drug therapy in acute lymphoblastic leukemia with a CXCR4 antagonist. Leukemia. 2011 Aug;25(8):1314-23. doi: 10.1038/leu.2011.76. Epub 2011 Apr 12. PubMed PMID: 21483439; PubMed Central PMCID: PMC3135709.

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11: Neves MA, Simões S, Sá e Melo ML. Ligand-guided optimization of CXCR4 homology models for virtual screening using a multiple chemotype approach. J Comput Aided Mol Des. 2010 Dec;24(12):1023-33. doi: 10.1007/s10822-010-9393-x. Epub 2010 Oct 20. PubMed PMID: 20960031.

12: De Clercq E. Recent advances on the use of the CXCR4 antagonist plerixafor (AMD3100, Mozobil™) and potential of other CXCR4 antagonists as stem cell mobilizers. Pharmacol Ther. 2010 Dec;128(3):509-18. doi: 10.1016/j.pharmthera.2010.08.009. Epub 2010 Sep 15. Review. PubMed PMID: 20826182.

13: Skerlj RT, Bridger GJ, Kaller A, McEachern EJ, Crawford JB, Zhou Y, Atsma B, Langille J, Nan S, Veale D, Wilson T, Harwig C, Hatse S, Princen K, De Clercq E, Schols D. Discovery of novel small molecule orally bioavailable C-X-C chemokine receptor 4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication. J Med Chem. 2010 Apr 22;53(8):3376-88. doi: 10.1021/jm100073m. PubMed PMID: 20297846.

14: Gudmundsson KS, Sebahar PR, Richardson LD, Miller JF, Turner EM, Catalano JG, Spaltenstein A, Lawrence W, Thomson M, Jenkinson S. Amine substituted N-(1H-benzimidazol-2ylmethyl)-5,6,7,8-tetrahydro-8-quinolinamines as CXCR4 antagonists with potent activity against HIV-1. Bioorg Med Chem Lett. 2009 Sep 1;19(17):5048-52. doi: 10.1016/j.bmcl.2009.07.037. Epub 2009 Jul 10. PubMed PMID: 19640718.

15: Moyle G, DeJesus E, Boffito M, Wong RS, Gibney C, Badel K, MacFarland R, Calandra G, Bridger G, Becker S; X4 Antagonist Concept Trial Study Team. Proof of activity with AMD11070, an orally bioavailable inhibitor of CXCR4-tropic HIV type 1. Clin Infect Dis. 2009 Mar 15;48(6):798-805. doi: 10.1086/597097. PubMed PMID: 19193109.

16: Wong RS, Bodart V, Metz M, Labrecque J, Bridger G, Fricker SP. Comparison of the potential multiple binding modes of bicyclam, monocylam, and noncyclam small-molecule CXC chemokine receptor 4 inhibitors. Mol Pharmacol. 2008 Dec;74(6):1485-95. doi: 10.1124/mol.108.049775. Epub 2008 Sep 2. PubMed PMID: 18768385.

17: Nyunt MM, Becker S, MacFarland RT, Chee P, Scarborough R, Everts S, Calandra GB, Hendrix CW. Pharmacokinetic effect of AMD070, an Oral CXCR4 antagonist, on CYP3A4 and CYP2D6 substrates midazolam and dextromethorphan in healthy volunteers. J Acquir Immune Defic Syndr. 2008 Apr 15;47(5):559-65. doi: 10.1097/QAI.0b013e3181627566. PubMed PMID: 18362694.

18: Cao YJ, Flexner CW, Dunaway S, Park JG, Klingman K, Wiggins I, Conley J, Radebaugh C, Kashuba AD, MacFarland R, Becker S, Hendrix CW. Effect of low-dose ritonavir on the pharmacokinetics of the CXCR4 antagonist AMD070 in healthy volunteers. Antimicrob Agents Chemother. 2008 May;52(5):1630-4. doi: 10.1128/AAC.01460-07. Epub 2008 Feb 19. PubMed PMID: 18285477; PubMed Central PMCID: PMC2346642.

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Additional Information

Related CAS#
558447-26-0 (free);
880549-30-4 (HCl)